Water → methyl 2-(1H-indazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

HRID 1405312Notes

Reaction equation

HRID 1405312 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[C:26]([N:27]([CH3:31])[CH:28]([CH3:30])[CH3:29])=[N:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:32]([O:34][CH3:35])=[O:33])[CH:23]=4)[N:18]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.O>ClCCl>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[C:26]([N:27]([CH3:31])[CH:28]([CH3:30])[CH3:29])=[N:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:32]([O:34][CH3:35])=[O:33])[CH:23]=4)[N:18]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 70654243methyl 2-[1-[(tert-butoxy)carbonyl]-1H-indazol-5-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate

Product 1

HCID 60171604methyl 2-(1H-indazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-[1-[(tert-butoxy)carbonyl]-1H-indazol-5-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (624 mg, 1.31 mmol) and trifluoroacetic acid (4 ml) in dichloromethane (20 ml) was stirred for 1 h at room temperature. The resulting solution was added water (200 ml) and adjusted to pH 8, extracted with dichloromethane (5×50 ml), dried over anhydrous magnesium and concentrated in vacuo to afford methyl 2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate as a yellow solid (442 mg, crude).

Workup

  1. extractionextracted with dichloromethane (5×50 ml)
  2. dry with materialdried over anhydrous magnesium
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7388e6fe10d04d2692cea8db3de7144b
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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